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BOC-D-SER-OME

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Products Intro: Product Name:N-BOC-D-serine methylester
CAS:95715-85-8
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Products Intro: Product Name:N-(tert-butoxycarbonyl)-D-serine methyl ester
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  • 2019-07-06
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BOC-D-SER-OME Basic information
Product Name:BOC-D-SER-OME
Synonyms:N-(TERT-BUTOXYCARBONYL)-D-SERINE METHYL ESTER;BOC-D-SERINE METHYL ESTER;BOC-D-SER-OME;D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester (9CI);N-(TERT-BBUTOXYCARBONYL)-L-SERINE METHYL ESTER;BOC-D-SERINE METHYLESTER OIL;N-BOC-D-serine methylester;N-BOC-D-ser-methylester
CAS:95715-85-8
MF:C9H17NO5
MW:219.24
EINECS:810-610-6
Product Categories:Pyridines;Chiral Reagents;Intermediates;Serine [Ser, S];Amino Acids & Derivatives;Amino Acid Derivatives;Peptide Synthesis;Serine;Heterocyclic Compounds;N-BOC
Mol File:95715-85-8.mol
BOC-D-SER-OME Structure
BOC-D-SER-OME Chemical Properties
Boiling point 215 °C(lit.)
density 1.08 g/mL at 25 °C(lit.)
refractive index n20/D 1.453(lit.)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform, Methanol
pka10.70±0.46(Predicted)
form Liquid
color Colorless to yellow
Optical Rotation[α]25/D +18.8°, c = 5 in methanol
Major Applicationpeptide synthesis
InChIInChI=1S/C9H17NO5/c1-9(2,3)15-8(13)10-6(5-11)7(12)14-4/h6,11H,5H2,1-4H3,(H,10,13)/t6-/m1/s1
InChIKeySANNKFASHWONFD-ZCFIWIBFSA-N
SMILESC(OC)(=O)[C@@H](CO)NC(OC(C)(C)C)=O
CAS DataBase Reference95715-85-8(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36/37/39
WGK Germany 3
HS Code 29241990
Storage Class10 - Combustible liquids
MSDS Information
ProviderLanguage
SigmaAldrich English
BOC-D-SER-OME Usage And Synthesis
Chemical Propertiescolorless to light yellow liquid
UsesProtected D-Serine.
reaction suitabilityreaction type: solution phase peptide synthesis
Synthesis
Di-tert-butyl dicarbonate

24424-99-5

2-AMINO-3-HYDROXY-PROPIONIC ACID METHYL ESTER

2104-89-4

BOC-D-SER-OME

95715-85-8

[Step 1] Synthesis of methyl (R)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropionate: To a solution of methanol (50 mL) containing methyl (R)-2-amino-3-hydroxypropionate (3.0 g, 19 mmol) and triethylamine (8.1 mL, 58 mmol) was slowly added di-tert-butyl dicarbonate (4.6 g, 21 mmol). The reaction mixture was stirred at room temperature for 14 h. The reaction was terminated by the addition of dilute hydrochloric acid. After continued stirring for 1 h, the reaction mixture was diluted with the addition of water and subsequently extracted with ethyl acetate. The organic layers were combined, washed sequentially with saturated aqueous sodium bicarbonate and pure water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent ratio: hexane/ethyl acetate=20:1→2:1) to afford 4.1 g (97% yield) of the title compound ((R)-2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoic acid methyl ester, hereinafter referred to as Reference Example compound 35).

References[1] Patent: EP2832724, 2015, A1. Location in patent: Paragraph 0186
[2] Tetrahedron Letters, 1995, vol. 36, # 39, p. 7031 - 7034
[3] Patent: WO2013/110643, 2013, A1. Location in patent: Paragraph 00104; 00105
[4] Tetrahedron, 1996, vol. 52, # 36, p. 11673 - 11694
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 923 - 928
Tag:BOC-D-SER-OME(95715-85-8) Related Product Information
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